Upon the death of his uncle Peyton Randolph in October 1775, Randolph returned to Virginia to act as executor of the estate, and while there was elected as a representative to the Virginia Convention. He would go on to serve as mayor of Williamsburg, and then as the first Attorney General of the United States under the newly formed government. He was married on August 29, 1776 to Elizabeth Nicholas (daughter of Robert C. Nicholas), and had a total of six children, including Peyton Randolph, Governor of Virginia from 1811 to 1812.[1]

Randolph was selected as one of eleven delegates to represent Virginia at the Continental Congress in 1779, and served as a delegate through 1782. During this period he also remained in private law practice, handling numerous legal issues for George Washington among others.

Randolph was elected Governor of Virginia in 1786, that same year leading a delegation to the Annapolis Convention. He had taken on the young John Marshall as a student and then law partner, and transferred his lucrative law practice to Marshall when he became governor in 1786, since Virginia law forbade executive officers from private practice in its courts.[2]

The following year, as a delegate from Virginia to the Constitutional Convention, Randolph introduced the Virginia Plan as an outline for a new national government.[3] He argued against importation of slaves and in favor of a strong central government, advocating a plan for three chief executives from various parts of the country. The Virginia Plan also proposed two houses, where in both of them delegates were chosen based on state population. Randolph additionally proposed, and was supported by unanimous approval by the Convention's delegates, "that a Nationally Judiciary be established" (Article III of the constitution established the federal court system).[4] The Articles of Confederation lacked a national court system for the United States.

Randolph was also a member of the "Committee of Detail" which was tasked with converting the Virginia Plan's 15 resolutions into a first draft of the Constitution.

Randolph ultimately refused to sign the final document, one of only three members who remained in the Constitutional Convention yet refused to sign (together with fellow Virginian George Mason and Elbridge Gerry of Massachusetts).[5] Randolph thought the final document lacked sufficient checks and balances, and published an account of his objections in October 1787. Randolph had several objections to the Convention’s proposal. He thought the federal judiciary would pose a threat to state courts, and he thought the Senate was too powerful and Congress’s power too broad.

Randolph nevertheless reversed his position at the Virginia Ratifying Convention in 1788. He chaired that nearly equally divided convention, and Mason (as one of the opposition leaders, along with Patrick Henry) greatly resented Randolph's change of position. Mason and other opponents demanded amendments prior to ratification. Randolph noted that he had seen several responses to the insistence that amendments were necessary before ratification. Some thought the objection insubstantial because the Constitution provided a process for amendment. In common with other advocates of amending the Constitution prior to ratification, Randolph insisted that it would be easier to amend the Constitution before ratifying it, when a majority might do so, than to ratify an imperfect Constitution and then assemble the votes of three-fourths of the states. He did not think it desirable that the people should become accustomed to altering their constitution with any regularity once it was adopted.

The Governor had written, “If after our best efforts for amendments, they cannot be obtained, I will adopt the constitution as it is.”[citation needed] Ultimately, Randolph said he voted for ratification of the Constitution because by June 2 eight other states had already done so, and he did not want to see Virginia left out of the new national government. Randolph believed that Virginia must choose between the stark alternatives of ratification and disunion. Randolph never doubted union's advantages.

Historians commonly have missed the signal importance of Randolph’s role in the Richmond Convention. In the Richmond Ratification Convention, it was Randolph who ultimately pointed the way to an understanding of ratification with which Virginia’s leaders could be satisfied. He assured his fellow members of the Virginia political elite that the Constitution they were being asked to ratify in the summer of 1788 would have very limited significance that it was more another league of sovereign states than a consolidated union they would be entering.

Randolph wrote that of the ten delegates whose views had been completely unknown, five had been swayed to vote for ratification by his gambit. In the end, Virginia’s Federalists secured the Constitution’s ratification by precisely five votes.

Washington rewarded Randolph for his support. Randolph was appointed as the first U.S. Attorney General in September 1789, maintaining precarious neutrality in the feud between Thomas Jefferson (of whom Randolph was a second cousin). In President Washington’s cabinet, as in the ratification dispute of 1787–1788, Randolph tried to find the mean, to bring people together, rather than jumping to a hasty conclusion and ignoring the potential costs in pursuit of self-righteous ideological purity.

When Jefferson resigned as Secretary of State in 1793, Randolph succeeded him to the position. The major diplomatic initiative of his term was the Jay Treaty with Britain in 1794, but it was Hamilton who devised the plan and wrote the instructions, leaving Randolph the nominal role of signing the papers. Randolph was hostile to the resulting treaty, and almost gained Washington's ear. Near the end of his term as Secretary of State, negotiations for Pinckney's Treaty were finalized.

Miss Nicholas was daughter of the Hon. Robert Carter Nicholas, State Treasurer. Randolph wrote to his children after his wife’s death. “We were both born in the city of Williamsburg, within twelve hours of each other; myself on the 10th of August 1753, and she on the 11th. My aunt Randolph, who saw each of us soon after our birth, facetiously foretold that we should be united in marriage-a circumstance which, improbable at the time from the dissensions of our families, seemed daily to grow into an impossibility from their increasing rancor. In childhood we were taught the elements of reading at the same school… she won me by the best of all graces, cheerfulness, good sense, and benevolence. I do not recollect that I reflected much upon that range of qualities, which I afterwards found to be constituents of nuptial happiness; but Providence seemed to be kinder to me than my most deliberate judgment could have been… I desired nothing more than that she should sincerely persuade herself that she would be happy with me.”

On the 29th day of August 1776 they were joined in wedlock. The relations between Randolph and his wife had always been true and tender. So free from friction had been the course of their united lives that his daughters could not forget the single instance of misunderstanding. Mrs. Randolph having related some incident, her husband hastily exclaimed: “That is mere gossip.” The lady repaired to her room, where she did not answer her husband’s gentle knock. Randolph then said “Betsey, I have urgent business in town, but I shall not leave this house until permitted to apologize to you.” The door opened and the unprecedented scene ends.

On the 6th of March 1810 came a blow from which Randolph could not recover; his wife died. After Mrs. Randolph’s burial the heart-broken husband wrote some account of her, and of their married life, which was addressed to his children as “the best witnesses of the truth of the brief history.”

In part of this account Randolph wrote, “My eyes are every moment beholding so many objects with which she was associated; I sometimes catch a sound which deludes me so much with the similitude of her voice; I carry about my heart and hold for a daily visit so many of her precious relics; and, above all, my present situation is so greatly contrasted by its vacancy, regrets, and anguish, with the purest and unchequred bliss, so far as it depended on her, for many years of varying fortune, that I have vowed at her grave daily to maintain with her a mental intercourse.”

A scandal involving an intercepted French message led to Randolph's resignation as Secretary of State in August, 1795. The British Navy had intercepted correspondence from the French minister, Joseph Fauchet, to the U.S. and turned it over to Washington. Washington was dismayed that the letters reflected contempt for the United States and that Randolph was primarily responsible. The letters implied that Randolph had exposed the inner debates in the cabinet to the French and told them that the Administration was hostile to France. At the very least, Elkins and McKitrick conclude, there "was something here profoundly disreputable to the government's good faith and character." Washington immediately overruled Randolph's negative advice regarding the Jay Treaty. A few days later Washington, in the presence of the entire cabinet, handed the minister's letter to Randolph and demanded he explain it. Randolph was speechless and immediately resigned. Chernow and Elkins[6][7] conclude that Randolph was not bribed by the French but "was rather a pitiable figure, possessed of some talents and surprisingly little malice, but subject to self-absorbed silliness and lapses of good sense." However, Randolph's own published Vindication illustrates his concerns regarding both public and private perceptions of his character, concerns which held great value in the 18th century.

Randolph County, West Virginia was formed in 1787 and named in Governor Randolph's honor.[9]Randolph County, Illinois was as well, because Randolph was Virginia's governor at the time it ceded what was then sometimes called Illinois County, Virginia (a title disputed by Pennsylvania, among others) to the new federal Government, which created the Northwest Territory. That Randolph county's motto is "where Illinois began," because it was among the first two settled counties in that territory, and contains Kaskaskia, which was first seat of Illinois County, later became the Illinois territory's capital and ultimately the state's first capital.